The Manager's Playbook

Generative AI is shaking up the music industry, creating new opportunities and new risks. In this clip, Isabel Quinteros (SVP at Jen Music AI and former Global Music Partnerships lead at TikTok) breaks down the ethical, legal, and cultural questions surrounding AI in music. From text-to-music prompts to copyright concerns, fair use, and artist compensation, Isabel shares how her team is building a...

In this episode, Mauricio Ruiz sits down with Isabel Quinteros, former Global Music Partnerships lead at TikTok and now SVP at Jen Music AI . From her start in PR to shaping TikTok’s rise and now leading conversations on AI, Isabel shares her journey and perspective on the future of music. They dive into the ethical challenges of AI, artist compensation, the role of blockchain in royalties, and ho...

After stepping away from music in 2015, Shawn Desman found himself questioning if he would ever return. In this conversation, he shares the pivotal moment with Drake that reignited his passion, the role his wife played in guiding crucial career decisions, and the challenges of navigating management changes. Alongside Steve Zsirai and Chad Walsh, Shawn also reveals the strategic and data-driven app...

Shawn Desman’s career looked finished, until it wasn’t. In this conversation, Shawn, Steve Zsirai, and Chad Walsh break down how a mix of social media strategy, data-driven decision-making, and the “Drake effect” helped spark one of the most inspiring comebacks in Canadian music. From TikTok virality to reconnecting with nostalgic fans, from analyzing where the audience actually lives to building...

What does it really take to build authentic relationships in music? In this conversation, Shawn Desman, Steve Zsirai, and Chad Walsh share why keeping a small, trusted circle is essential, how empathy and honesty drive lasting partnerships, and why boundaries matter in an industry that often blurs the personal with the professional. Shawn also reflects on how personal struggles, including overcomi...

What makes a great artist, and a great manager? In this conversation, Shawn Desman, Steve Zsirai, and Chad Walsh break down the traits that separate the good from the unforgettable. From delivering “the good stuff” right away to the power of live performance and the rare quality of time feel , they share what truly moves audiences. The discussion also touches on lessons from Beyoncé, Coldplay, Dra...

Shawn Desman’s story is one of highs, lows, and a powerful comeback. From topping the charts to stepping away from music, Shawn opens up about the pressure of fame, battling depression, and finding sobriety. With Drake’s encouragement at an OVO event, he rediscovered his love for music and returned on his own terms. Alongside managers Steve Zsirai and Chad Walsh, the conversation dives into the st...

In this clip from The Manager’s Playbook , Mauricio Ruiz speaks with Milana Lewis (CEO of Stem) about her journey from having no background in music to becoming a leading entrepreneur in the industry. Milana explains how building around clear vision and values , and using frameworks like EOS (Entrepreneurial Operating System), helped her align her company. She shares why the right team matters mor...

In this clip from The Manager’s Playbook , Mauricio Ruiz sits down with Milana Lewis (CEO of Stem) to unpack the realities of artist development and partnerships in today’s music business. Milana shares how artists can get noticed without relying solely on social media, why consistent storytelling is key, and the tough decisions behind who gets signed and when. She also dives into the challenges o...

In this clip from The Manager’s Playbook , Mauricio Ruiz sits down with Milana Lewis, CEO of Stem , to break down how Stem approaches artist partnerships and deal-making differently. Milana explains why Stem works on a project-by-project basis , how they manage capacity to protect quality, and how their simulator tool helps artists actually understand the financial reality of a deal. She also unpa...

In this clip from The Manager’s Playbook , Mauricio Ruiz sits down with Milana Lewis, CEO & Co-Founder of Stem , to break down one of the music industry’s biggest flaws: royalty accounting. Milana shares how Stem set out to simplify payments, give artists clarity on what they own, and make sure money flows where it should. She also explains the early challenges of distribution, the struggles Y...

In episode 39 of The Manager’s Playbook , Mauricio Ruiz sits down with Milana Lewis, co-founder and CEO of STEM , to unpack the realities of today’s music business. Milana explains why royalty accounting is still one of the industry’s biggest problems, why so many artists don’t know what they own or when they’ll get paid, and how that lack of clarity gets exploited in bad deals. She also breaks do...

In this clip from  The Manager’s Playbook , Rich Castillo pulls back the curtain on the realities of A&R and the inner workings of major labels. He explains how decisions actually get made inside the hierarchy, the role data plays in scouting talent, and why live shows still matter in discovering artists. We also explore how young A&R execs can grow within the system, the pressure IPOs put...

In this clip from  The Manager’s Playbook , Rich Castillo dives into the rise of UK rap culture and its global impact. He explains how London’s melting pot of influences creates a distinct sound, why regional identity is crucial for artists, and how UK rap compares to the U.S. scene. Rich also shares his personal journey, from early career setbacks and getting fired to thriving as an executive, wo...

In this clip from  The Manager’s Playbook , Rich Castillo reflects on his move from the major label system to launching his own independent label,  Lion Bear . He shares why legacy and independence matter more than comfort, what inspired him to take control of his career, and how he’s thinking about the next chapter of the music business. Rich also introduces his new podcast,  The Hot Seat , desig...

In this clip from  The Manager’s Playbook , Rich Castillo breaks down what the role of A&R really looks like in 2025. From identifying and developing talent to balancing data, instinct, and marketing, Rich shares how decisions actually get made inside labels. We also discuss the traits that separate great A&R executives from the rest, the misconceptions around the job, and the pitfalls art...

Rich Castillo has spent nearly two decades inside the music industry, from Polydor, Sony, and EMI to Warner and now his own company, Lion Bear. In this episode of The Manager’s Playbook , Rich breaks down what A&R really means in 2025, why most artists lose urgency after signing, and how to navigate label politics without losing your vision. We also dive into artist development, the tug-of-war...

In this conversation, Jared Cotter and I dig into what it really takes to build a modern superstar. We talk about the rise of Shaboozey, how undeniable talent meets the right strategy, and the pivotal role management plays in turning momentum into long-term success. From building strong teams to navigating industry shifts, Jared shares the lessons that matter most for artists and managers alike. I...

In this conversation, Jared Cotter and I dig into the journey of breaking into country music and why authenticity always wins. We talk about how Shaboozey carved out his space in Nashville, the importance of diversity and representation, and how the genre is slowly opening its doors to new voices. Jared shares stories of resilience, community, and the impact of artists who are breaking barriers an...

In this conversation, Jared Cotter and I dig into the world of music publishing and what it really takes to build a sustainable career. Jared shares his perspective as both a songwriter and a manager — from the smartest types of publishing deals to the importance of choosing the right partners. We talk about long-term strategy versus short-term checks, how to balance business with creativity, and...

In this conversation, Jared Cotter and I break down the making of Shaboozey’s “A Bar Song (Tipsy).” We talk about the creative spark, the key moments that shaped the record, and what it takes to recognize when you’ve got a hit on your hands. From the late-night studio energy to the strategy behind pushing it forward, this is a candid look at how an idea turned into one of the biggest independent r...

Jared Cotter is the manager behind one of the biggest independent success stories of the decade. In this episode, we talk about how Shaboozey’s “A Bar Song (Tipsy)” made history, spending 19 weeks at #1 and tying the record set by Lil Nas X’s “Old Town Road” . But unlike most chart-toppers, this run happened completely independent, through Empire and his record label, American Dogwood. Jared share...

In this episode of The Manager’s Playbook , publicist Loren Medina unpacks the evolving music industry and what independence really means for artists today. She challenges the myth that signing to a label guarantees success, pointing to examples like Bad Bunny to show how ownership and freedom have reshaped the game. Loren shares practical strategies for building PR from scratch, crafting effectiv...

In this clip of The Manager’s Playbook , publicist Loren Medina talks about what it’s really like to work with record labels from the outside. She explains why so many label teams lack long-term strategy, even for major artists, and how her structured approach sets her apart. Loren shares her experience promoting Jessie Reyez in both English and Latin markets, reflects on the importance of humilit...

In this clip of The Manager’s Playbook , publicist Loren Medina shares her journey from leaving Sony to launching Digital Girl in 2009, one of the first social media marketing companies in music. She reflects on navigating the early days of digital marketing, the importance of innovation and branding, and how those experiences shaped her move into PR. Loren also opens up about the realities of the...